FComEx: Hippuric acid (PC000158)

Record Information

Version

1.0

Creation date

2015-10-09 22:28:54 UTC

Update date

2017-01-19 02:36:15 UTC

FoodComEx ID

PC000158

FoodDB Record

FDB001819

Chemical Information

Name

Hippuric acid

Description

Hippuric acid (Gr. hippos, horse, ouron, urine) is a carboxylic acid found in the urine of horses and other herbivores. Hippuric acid crystallizes in rhombic prisms which are readily soluble in hot water, melt at 187 °C and decompose at about 240 °C. High concentrations of hippuric acid can also indicate a toluene intoxication. When many aromatic compounds such as benzoic acid and toluene are taken internally, they are converted to hippuric acid by reaction with the amino acid, glycine.; Hippuric acid is an acyl glycine formed by the conjugation of benzoic aicd with glycine. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction: acyl-CoA + glycine < -- > CoA + N-acylglycine. Hippuric acid is a normal component of urine and is typically increased with increased consumption of phenolic compounds (tea, wine, fruit juices). These phenols are converted to benzoic acid which is then converted to hippuric acid and excreted in the urine. Hippuric acid is the most frequently used biomarker in the biological monitoring of occupational exposure to toluene. This product of solvent biotransformation may be also found in the urine of individuals who have not been exposed to the solvent. A smaller fraction of the absorbed toluene is oxidized to aromatic compounds including ortho-cresol, which is not found significantly in the urine of nonexposed individuals. The concentration of hippuric acid in the urine of individuals exposed to a low toluene concentration does not differ from that of individuals not exposed to the solvent. This has led to the conclusion that hippuric acid should not be utilized in the biological monitoring of occupational exposure to low levels of toluene in the air.; Protein-bound organic acids such as hippuric acid are markedly accumulated in uremic plasma and produce defective protein binding of drugs. (PMID: 9120876, 8734460).

CAS Number

495-69-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(benzoylamino)-acetate	biospider
(benzoylamino)-acetic acid	biospider
(benzoylamino)acetic acid	biospider
2-benzamido-acetic acid	biospider
2-Benzamidoacetate	biospider
2-Benzamidoacetic acid	biospider
532-93-4 (mono-ammonium salt)	biospider
532-94-5 (mono-hydrochloride salt)	biospider
583-10-8 (mono-potassium salt)	biospider
Acetic acid, (benzoylamino)-	biospider
Acetic acid,benzamide hippuric acid	biospider
Acido ippurico	biospider
Benzamidoacetate	biospider
Benzamidoacetic acid	biospider
Benzaminoacetic acid	biospider
Benzenecarboxamide, n-carboxymethyl-	biospider
Benzoylaminoacetic acid	biospider
Benzoylglycin	biospider
Benzoylglycine	biospider
Benzoylglycocoll	biospider
Glycine, n-benzoyl-	biospider
Hippurate	biospider
Hippuricum acidum	biospider
N-(phenylcarbonyl)glycine	biospider
N-benzoyl-glycin	biospider
N-benzoylglycine	biospider
Phenylcarbonylaminoacetate	biospider
Phenylcarbonylaminoacetic acid	biospider

Chemical Formula

C9H9NO3

IUPAC name

2-(phenylformamido)acetic acid

InChI Identifier

InChI=1S/C9H9NO3/c11-8(12)6-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)

InChI Key

QIAFMBKCNZACKA-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)CNC(=O)C1=CC=CC=C1

Average Molecular Weight

179.1727

Monoisotopic Molecular Weight

179.058243159

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents

Substituents

Hippuric acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Benzoyl
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

N-acylglycine (CHEBI:18089 )

Physico-Chemical Properties - Experimental

Property	Value	Reference
Experimental logP	0.31	HANSCH,C ET AL. (1995)
Experimental Water Solubility	3.75 mg/mL at 25 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Melting Point	187-191 oC

Foods of Origin